Ethyl 3-oxo-4-phenylbutanoate CAS 718-08-1

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April 24, 2025

Ethyl 3-oxo-4-phenylbutanoate occupies a curious niche in olfactory deception strategies for pest control, where its fruity, caramel-like aroma is being repurposed to disrupt insect chemoreception in agricultural systems. Unlike conventional pheromone traps, this β-keto ester selectively masks the scent trails of invasive ant species (e.g., Linepithema humile) by saturating their 9-ODA receptors, effectively creating "chemical smog" that prevents colony coordination. In an unexpected twist, mycology researchers have discovered its role as a volatile priming agent for basidiomycete fungi-when vaporized near Pleurotus spp. mycelia, it triggers a 3-fold increase in extracellular ligninolytic enzymes through an unknown β-oxidation signaling pathway, potentially revolutionizing low-cost substrate pretreatment for mushroom farming. Even more esoterically, marine chemists are investigating its **coral stress response modulation*; when microencapsulated in pH-sensitive hydrogels, it appears to mitigate bleaching in Acropora spp. by competitively inhibiting zooxanthellae lipid peroxidation, though the exact mechanism remains elusive. The compound's recently observed supramolecular behavior in non-polar solvents-forming helical aggregates that catalyze [4+2] cycloadditions under blue light-adds another layer of peculiar utility in abiotic chemical synthesis. These disparate applications reveal Ethyl 3-oxo-4-phenylbutanoate as a molecular multitool, bridging entomology, mycology, marine biology, and materials science through its versatile reactivity and sensory profile.

Ethyl 3-oxo-4-phenylbutanoate, also known as 4-phenylacetoacetate ethyl ester, is a widely used synthetic intermediate. Its chemical formula is C12H14O3 and its molecular weight is 206.24, demonstrating significant application value in multiple fields.

1. Synthesis of pyrazolone derivatives

 

Plays a crucial role in drug synthesis, particularly in the preparation of pyrazolone derivatives. Pyrazolone compounds have a wide range of biological activities, some of which have been shown to have anti prion activity. Prions are a type of infectious factor composed solely of proteins without nucleic acid, and are associated with various neurodegenerative diseases such as Creutzfeldt Jakob disease and Kuru disease. By synthesizing pyrazolone derivatives, scientists have provided new drug candidates for the treatment of these diseases.

2. Preparation of Pyrrolidine Pyrimidine Analogues

 

In addition, it can also be used to prepare pyrrolidine pyrimidine analogues. These compounds are of great significance in biomedical research as they can act as inhibitors of AP-1 (activator protein-1) and NF - κ B (nuclear factor kappa B) - mediated gene expression. AP-1 and NF - κ B are two important transcription factors involved in regulating various cellular processes, including inflammatory response, cell proliferation, and apoptosis. By inhibiting the activity of these transcription factors, pyrrolidine pyrimidine analogs may provide a new strategy for treating inflammatory diseases, cancer, and other conditions.

1. Organic synthesis raw materials

 

As an important raw material for organic synthesis, it has a wide range of applications in the chemical industry. It can participate in various chemical reactions, such as esterification, condensation, oxidation, etc., to generate compounds with specific structures and properties. These compounds have potential application value in fields such as pesticides, dyes, fragrances, plastics, etc.

2. Polymer material modifier

 

In the field of polymer materials, it can be used as a modifier. By introducing it into polymer chains, the physical and chemical properties of polymer materials can be altered, such as improving heat resistance, weather resistance, mechanical strength, etc. This modification method provides a new approach for the functionalization and high-performance of polymer materials.

1. Biological activity research

 

This substance and its derivatives have potential application value in biomedical research. Through in-depth research on its biological activity, scientists can reveal the life processes it participates in and explore its potential as a drug candidate. For example, studies have shown that certain pyrazole derivatives have anti-inflammatory, antioxidant, anti-tumor and other activities, providing important clues for the development of new drugs.

2. Regulation of cellular signal transduction

 

This substance and its derivatives may also participate in cellular signaling processes in biomedical and its analogues. Cellular signaling is one of the important regulatory mechanisms of life activities, involving the interaction of multiple signaling molecules and the activation or inhibition of signaling pathways. By regulating these signaling pathways, cell proliferation, differentiation, apoptosis, and other processes can be influenced, providing new strategies for treating related diseases.

1. Chemical experiment teaching

 

In chemistry education, it can serve as an important material for experimental teaching. By synthesizing and characterizing the compound, students can master the basic operations and skills of organic chemistry, such as esterification reactions, separation and purification, structural characterization, etc. Meanwhile, this compound can also be used as a case study to explain the basic concepts and principles of organic chemistry, such as functional groups, stereoisomers, reaction mechanisms, etc.

2. Support for scientific research projects

 

In scientific research projects, it can be used as a research object or tool molecule. Through in-depth research on its synthesis methods, structural characteristics, biological activities, and other aspects, new ideas and methods can be provided for scientific research in related fields. In addition, the compound can also be used as a probe or marker for experiments such as cell imaging and protein interaction analysis in biomedical research.

1. Exploration of green synthesis methods

 

With the increasing awareness of environmental protection and the promotion of sustainable development concepts, green synthesis methods have become one of the important directions in current chemical research. Traditional synthesis methods typically require anhydrous conditions, long reaction times, complex operations, and low product yields. Therefore, exploring more environmentally friendly and efficient synthesis methods is of great significance for achieving sustainable production of this compound.

2. Waste disposal and resource recycling

 

In the industrial production process, the waste disposal of this substance and its related compounds is also a matter of concern. By implementing reasonable waste management strategies and resource recycling technologies, environmental pollution and resource waste can be reduced. For example, chemical or biological methods can be used to convert waste into valuable compounds or energy, thereby achieving resource recycling.

3. Biomedical Engineering Applications

 

In the field of biomedical engineering, this substance and its analogues may also have potential application value. For example, it can be used as a drug carrier or targeted molecule for drug delivery systems in disease treatment; Alternatively, it can be used as a biosensor or biomarker for disease diagnosis or monitoring of biological processes. The exploration of these application fields will provide new ideas and methods for the development of biomedical engineering.

Ethyl 3-oxo-4-phenylbutanoate is widely and deeply used in the pharmaceutical industry, and its unique chemical structure and pharmacological properties make it an important pharmaceutical ingredient or research tool for treating various diseases.

 

1. Treatment of neurological disorders

It has shown significant efficacy in treating neurological disorders, especially for nerve conduction disorders such as multiple sclerosis (MS). Multiple sclerosis is a chronic disease that affects the central nervous system, leading to demyelination of nerve fibers and axonal damage, thereby affecting the transmission of nerve signals. It can inhibit voltage-gated potassium channels, enhance neuronal excitability, and improve nerve conduction function.

Specific examples include:
A study on patients with multiple sclerosis found that taking medication can significantly improve their walking ability and quality of life. This medication can reduce patients' fatigue, improve exercise endurance and balance ability.
It is also used to treat other neurological diseases such as Parkinson's disease, spinal cord injury, etc. In these diseases, it is also possible to improve nerve conduction function and promote the recovery and regeneration of neurons.

 

2. Tool compounds in neuroscience research

As an important tool compound in neuroscience research, it is used to understand the functions of neuronal pathways and ion channels. Ion channels are important proteins on the neuronal cell membrane that regulate the transmembrane flow of ions, thereby controlling the excitability and conductivity of neurons. It can specifically inhibit certain types of potassium ion channels, thereby altering the electrophysiological properties of neurons.

Specific examples include:
Researchers use it to study the synaptic transmission process between neurons. By inhibiting potassium ion channels, the release of neurotransmitters can be increased, thereby enhancing the excitability of postsynaptic neurons. This helps to reveal the mechanisms and regulatory mechanisms of information transmission between neurons.
It is also used to study the pathogenesis and treatment methods of neurodegenerative diseases. By inhibiting potassium ion channels, the degeneration and death process of neurons can be slowed down, providing new ideas and methods for treating these diseases.

 

3. Improve acute axonal injury and demyelinating degeneration

Significant therapeutic effects have also been demonstrated in the treatment of acute axonal injury and demyelinating degeneration. Axon injury and demyelinating degeneration are common pathological features of various neurological diseases, including traumatic brain injury (TBI), spinal cord injury, etc. It can inhibit abnormal potassium channels in axons, enhance the conduction of electrical action potentials, and regulate neural circuits, thereby promoting the structural recovery of axons and myelin sheaths.

Specific examples include:
A study on mice with traumatic brain injury found that taking it can significantly improve axonal swelling and demyelination in mice. This drug can reduce the number of spherical swelling caused by axonal rupture, promote the recovery and regeneration of axons and myelin sheaths.
It is also used to treat patients with spinal cord injury. By inhibiting potassium ion channels, the regeneration and repair of spinal cord neurons can be promoted, thereby improving the motor and sensory functions of patients.

3-Oxo-4-phenylbutanoate ethyl ester, also known as 4-phenylacetoacetate ethyl ester, English name: 3-Oxo-4-phenylbutanoate ethyl ester, CAS number: 718-08-1, molecular formula: C12H14O3, Molecular weight: 206.23800. 3-Oxo-4-phenylbutanoic acid ethyl ester is a useful synthetic intermediate. It is used to prepare pyrazolone derivatives as antiviral compounds. It is also used to prepare pyrrolopyrimidine analogs as inhibitors of AP-1 and NF - κ B-mediated gene expression.

The traditional synthesis method of 3-Oxo-4-phenylbutanoate ethyl ester is to prepare it in anhydrous ethanol using ethyl acetoacetate and halogenated hydrocarbons as raw materials, under the action of metal sodium or sodium acetate. This method has strict conditions, and the reaction needs to be carried out under completely anhydrous conditions, with long reaction time, complex operation, and low product yield. This article uses ethyl acetoacetate and phenylacetyl chloride as starting materials to prepare 3-Oxo-4-phenylbutanoate ethyl ester through continuous reaction. The synthesis reaction formula is shown in the following figure:

(1) Firstly, prepare a mixture of ethyl acetoacetate and dichloromethane containing phenylacetyl chloride in a certain proportion. Then, continuously inject the mixture and thionyl chloride into the microchannel reactor at a certain flow rate using a metering pump, and control the outlet temperature of the reactor to 5-10 ℃; Then mix the prepared saturated saline solution continuously with the reaction solution in layers, with the lower layer being the reaction solution and the upper layer being the saline solution.

(2) Under normal pressure, slowly raise the temperature of the washed reaction solution. When the bottom temperature reaches 55 ℃, dichloromethane begins to evaporate until the bottom temperature reaches 100 ℃ (ensuring complete evaporation of the solvent). Stop heating and collect the distilled solvent by cooling;

(3) After recovering the solvent, vacuum distillation was carried out at a vacuum degree of -0.1 MPa, and the temperature was slowly increased. When the kettle temperature was 85-90 ℃, the reflux ratio was controlled at 4, and the finished product began to evaporate. When the kettle temperature reached 120 ℃, the heating was stopped and the vacuum pump was turned off to obtain the qualified finished product ethyl 3-oxo-4-phenylbutanoate, and its chromatographic content was measured.

Ethyl 3-oxo-4-phenylbutanoate is an important organic synthetic intermediate widely used in the fields of pharmaceuticals, fragrances, and fine chemicals. As a β - ketoester compound, its molecular structure contains ketone, ester, and phenyl groups simultaneously, making it a key precursor for the synthesis of various complex molecules. The research on β - ketoester compounds can be traced back to the golden age of organic chemistry in the 19th century:

At the beginning of the 20th century, chemists began exploring phenyl substituted β - ketoesters:

• The introduction of benzene ring can change the electron distribution and affect the reaction activity
• Aromatic β - ketoesters may have special biological activity
• As a potential intermediate for synthesizing complex aromatic compounds

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